Patent GB-773431-A (GB)
Title: Compositions comprising halogenated octahydro-endo, endo-dimethano-naphthalenes and stabiliser therefor
IPC: C07D303/10
Filed: 1955-05-02
Abstract: The invention comprises a composition containing a halogen-epoxy octahydro-eudo-eudo-dimethanonaphthalene or an alkyl, alkoxy, or ester derivative thereof and, as stabilizer a small proportion of an acid-binding agent and/or an iron complex forming agent.  In examples, the 6:7 - epoxy - 1:2:3:4:10:10 - hexa - chloro-1:4:4a:5:6:7:8:8a - octahydro - 1:4:5:8 - endo - endo - dimethanonaphthalene, generally commercial product, is stabilized with solid sodium carbonate, solid potassium hydroxide, and in solution in benzene, with thiourea, urea potassium thiocyanate, tetrasodium ethylene diamine tetra-acetic acid, sodium N:N-di-2-hydroxyethyl glycine guanidine carbonate, diisopropyl ammonium nitrite phenyl glycidyl ether and allyl glycidyl ether followed generally by evaporating to dryness, and in acetone solution with epichlorhydrin.  The compounds which may be stabilized have the general formula <FORM:0773431/IV(b)/1> in which X is Cl or Br and Y is H, alkyl, alkoxy or ester group. Generally, other stabilizers specified, include alkaline-reacting salts of alkali metals, such as the salts of weak acids, alkaline reacting compounds of the alkaline earths, nitrogenous bases such as quaternary ammonium hydroxides, tertiary amines, and especially normally solid bases and their salts; the following nitrites of nitrogenous bases: heterocyclic, secondary and tertiary amines; urea, thiourea and N-substituted ureas; alkali metal salts of alkyl substituted phenols and aldehyde-alkylphenol condensation products of molecular weight about 350-2000, in which the alkyl group in para-position may have 5-20 carbon atoms and the aldehydes may be up to butyraldehyde and also acrolein; phenolic salts containing carboxylic groups, and higher alkyl groups with alkali metal bases present in excess; epoxy compounds and halogen substitution products thereof, and also containing additional oxygen atoms as in ether groups, e.g. numerous glycidyl ethers including ethylene glycol diglycidyl ether, resorcinol diglycidyl ether and bis-phenol diglycidyl ethers, also glycidyl esters of fatty acids. Other iron-complex forming agents specified in addition include compounds containing cyanide and cyanate ions, and compounds which give polydentate addenda and are capable of chelating the ferric ion, e.g. geminate dicarboxylic acids, such as oxalic acid, ethylene diamine and methylene triamine and their derivatives, aromatic heterocyclic polyamines, such as dipyridyl and o-phenanthroline, many amino acids, and their partial salts, or inner salts, and containing a plurality of nitrogen and/or carboxyl groups, e.g. ammonia polyacetic acids, 3-sulphoaniline diacetic acid, b -amino ethylphosphonic acid N : N-diacetic acid, and diamine di-fatty acids; and finally polyfunctional compounds acting both as acid-binding and iron complex forming agents including hydroxy-amino-acids and their salts, e.g. N - 2 - hydroxyethylimino - diacetic acid and many others, especially N : N-dihydroxy-ethylglycine alkali metal salt. The stabilizers for which several general formul  are given, prevent the rapid decomposition of " endrin " compounds as in the examples, due to the presence of traces of iron, and to their structure.